CN105165883A - Fungicidal Mixtures Based On Azolopyrimidinylamines - Google Patents

Fungicidal Mixtures Based On Azolopyrimidinylamines Download PDF

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CN105165883A
CN105165883A CN201510595181.1A CN201510595181A CN105165883A CN 105165883 A CN105165883 A CN 105165883A CN 201510595181 A CN201510595181 A CN 201510595181A CN 105165883 A CN105165883 A CN 105165883A
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methyl
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C·贝克
M·尼登布吕克
M·舍勒尔
R·施蒂尔
S·施特拉特曼
U·许格尔
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BASF SE
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system

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Abstract

Fungicidal mixtures comprising as active components 1) azolopyrimidinylamines of the formula I in which the substituents are defined as in the description and 2) at least one active compound II selected from the following groups: azoles, strobilurins, carboxamides, heterocylic compounds, carbamates and other active compounds, selected from guanidines, antibiotics, sulphur-containing heterocyclyl compounds, organophosphorus compounds, organochlorine compounds, inorganic active compounds, growth retardants and cyflufenamid, cymoxanil, dimethirimol, ethirimol, furalaxyl, metrafenone and spiroxamine; in a synergistically effective amount. Methods of controlling fungal pathogens using mixtures of the compound I with active compounds II, and the use of the compound I with active compounds II for producing such mixtures, and also compositions comprising these mixtures.

Description

Based on azoles and the Fungicidal mixture of pyrimidine radicals amine
The divisional application of the patent application that the application is application number is 201310070474.9, the applying date, to be July 20, denomination of invention in 2006 be " based on azoles and the Fungicidal mixture of pyrimidine radicals amine ".
Application number is the divisional application of the patent application that patent application be application number is 200680027402.4, the applying date, to be July 20, denomination of invention in 2006 be " based on azoles and the Fungicidal mixture of pyrimidine radicals amine " of 201310070474.9.
The present invention relates to Fungicidal mixture, it comprises following compound as active component using Synergistic effective dose:
1) azoles of at least one formula I pyrimidine radicals amine:
Wherein each substituting group defined as follows:
R 1for C 3-C 12alkyl, C 2-C 12alkenyl, C 5-C 12alkoxyalkyl, C 3-C 6cycloalkyl, benzene
Base or phenyl-C 1-C 4alkyl;
R 2for C 1-C 12alkyl, C 2-C 12alkenyl, C 1-C 4haloalkyl, C 1-C 4alkoxy-C 1-C 4alkyl;
Wherein R 1and/or R 2in aliphatic chain can by the identical or different radicals R of 1-4 areplace:
R afor halogen, cyano group, hydroxyl, sulfydryl, C 1-C 10alkyl, C 1-C 10haloalkyl, C 3-C 8cycloalkyl, C 2-C 10alkenyl, C 2-C 10alkynyl, C 1-C 6alkoxyl, C 1-C 6alkylthio group, C 1-C 6alkoxy-C 1-C 6alkyl or NR ar b;
R a, R bfor hydrogen and C 1-C 6alkyl;
Wherein R 1and/or R ain cyclic group can by 1-4 radicals R breplace:
R bfor halogen, cyano group, hydroxyl, sulfydryl, nitro, NR ar b, C 1-C 10alkyl, C 1-C 6haloalkyl, C 2-C 6alkenyl, C 2-C 6alkynyl or C 1-C 6alkoxyl;
R 3for hydrogen, halogen, cyano group, NR ar b, hydroxyl, sulfydryl, C 1-C 6alkyl, C 1-C 6haloalkyl, C 3-C 8cycloalkyl, C 1-C 6alkoxyl, C 1-C 6alkylthio group, C 3-C 8cycloalkyloxy, C 3-C 8cycloalkylthio, carboxyl, formoxyl, C 1-C 10alkyl-carbonyl, C 1-C 10alkoxy carbonyl group, C 2-C 10chain ene keto carbonyl, C 2-C 10alkynes oxygen carbonyl, phenyl, phenoxy group, thiophenyl, benzyloxy, benzylthio, C 1-C 6alkyl-S (O) m-;
M is 0,1 or 2;
A is CH or N;
With
2) at least one is selected from the reactive compound II of lower group:
A) azole, as Bitertanol (bitertanol), bromuconazole (bromuconazole), cyproconazole (cyproconazole), ether azoles (difenoconazole), olefin conversion (diniconazole), IMAZALIL (enilconazole), oxole bacterium (epoxiconazole), Fluquinconazole (fluquinconazole), RH-7592 (fenbuconazole), Flusilazole (flusilazole), Flutriafol (flutriafol), own azoles alcohol (hexaconazole), acid amides azoles (imibenconazole), cycltebuconazole (ipconazole), ring penta azoles bacterium (metconazole), nitrile bacterium azoles (myclobutanil), penconazole (penconazole), propiconazole (propiconazole), prothioconazoles (prothioconazole), simeconazoles (simeconazole), triazolone (triadimefon), triadimenol (triadimenol), Tebuconazole (tebuconazole), fluorine ether azoles (tetraconazole), triticonazole (triticonazole), Prochloraz (prochloraz), pefurazoate (pefurazoate), IMAZALIL (imazalil), fluorine bacterium azoles (triflumizole), cyazofamid (cyazofamid), benomyl (benomyl), carbendazim (carbendazim), thiabendazole (thiabendazole), furidazol (fuberidazole), Guardian (ethaboxam), kobam (etridiazole), hydroxyisoxazole (hymexazole),
B) strobilurins class (strobilurins), as nitrile Fluoxastrobin (azoxystrobin), dimoxystrobin (dimoxystrobin), Enestroburin (enestroburin), fluoxastrobin (fluoxastrobin), imines bacterium (kresoxim-methyl), fork phenalgin acid amides (metominostrobin), orysastrobin (orysastrobin), ZEN 90160 (picoxystrobin), pyraclostrobin (pyraclostrobin), oxime bacterium ester (trifloxystrobin) or (the chloro-5-of 2-[1-(3-methyl-benzyloxyimino) ethyl] benzyl) methyl carbamate, (the chloro-5-of 2-[1-(6-picoline-2-base methoxyimino) ethyl] benzyl) methyl carbamate, 2-(o-(2, 5-dimethylphenyloxymethylene) phenyl)-3-methoxy-methyl acrylate,
C) carboxylic acid amides, as carboxin (carboxin), M 9834 (benalaxyl), Boscalid (boscalid), fenhexamid (fenhexamid), flutolanil (flutolanil), furan pyrazoles spirit (furametpyr), the third oxygen go out embroider amine (mepronil), metalaxyl (metalaxyl), Metalaxyl-M (mefenoxam), fenfuram (ofurace), frost spirit (oxadixyl), oxycarboxin (oxycarboxin), pyrrole metsulfovax (penthiopyrad), thifluzamide (thifluzamide), tiadinil (tiadinil), N-(4 '-bromo biphenyl-2-base)-4-difluoromethyl-2-methylthiazol-5-formamide, N-(4 '-trifluoromethyl-biphenyl-2-base)-4-difluoromethyl-2-methylthiazol-5-formamide, N-(4 '-chloro-3 '-fluorine biphenyl-2-base)-4-difluoromethyl-2-methylthiazol-5-formamide, N-(3 ', 4 '-two chloro-4-fluorine biphenyl-2-base)-3-difluoromethyl-1-methylpyrazole-4-formamide, N-(3', 4'-bis-chloro-5-fluorine biphenyl-2-base)-3-difluoromethyl-1-methylpyrazole-4-formamide, the chloro-N-of 3,4-bis-(2-cyano-phenyl) isothiazole-5-formamide, dimethomorph (dimethomorph), flumorph (flumorph), fluorine biphenyl bacterium (flumetover), fluopicolide (picobenzamid), zoxamide (zoxamide), carpropamide (carpropamid), two chlorine zarilamid (diclocymet), mandipropamid (mandipropamid), N-(2-{4-[3-(4-chlorphenyl) third-2-alkynyloxy group]-3-anisyl } ethyl)-2-methanesulfonamido-3-methylbutyryl amine, N-(2-{4-[3-(4-chlorphenyl)-propyl-2-alkynyloxy group]-3-anisyl } ethyl)-2-second sulfonamido-3-methylbutyryl amine,
D) following heterocyclic compound is selected from: fluazinam (fluazinam), pyrifenox (pyrifenox), the phonetic bacterium spirit (bupirimate) of sulphur, ring third pyrimidine (cyprodinil), fenarimol (fenarimol), ferimzone (ferimzone), mepanipyrim (mepanipyrim), nuarimol (nuarimol), pyrimethanil (pyrimethanil), triforine (triforine), fenpiclonil (fenpiclonil), fluorine bacterium (fludioxonil), 4-dodecyl-2,6-thebaine (aldimorph), dodemorfe (dodemorph), butadiene morpholine (fenpropimorph), tridemorph (tridemorph), fenpropidin (fenpropidin), isopropyl fixed (iprodione), sterilization profit (procymidone), vinclozolin (vinclozolin), famoxadone (famoxadone), Fenamidone (fenamidone), different thiophene bacterium ketone (octhilinone), probenazole (probenazole), amisulbrom (amisulbrom), anilazine (anilazine), diclomezine (diclomezine), pyroquilon (pyroquilon), third oxygen quinoline (proquinazid), tricyclazole (tricyclazole), the chloro-7-of 5-(4-methyl piperidine-1-base)-6-(2, 4, 6-trifluorophenyl) [1, 2, 4] triazol [1, 5-a] pyrimidine, 2-butoxy-6-iodo-3-propyl group chromene-4-ketone, thiadiazoles element (acibenzolar-S-methyl), difoltan (captafol), captan (captan), dazomet (dazomet), folpet (folpet), zarilamid (fenoxanil), quinoxyfen (quinoxyfen), 3-[5-(4-chlorphenyl)-2, 3-dimethyl is different azoles alkane-3-base] pyridine,
E) Carbamates, as mancozeb (mancozeb), maneb (maneb), metham-sodium (metam), Carbatene (metiram), ferbam (ferbam), propineb (propineb), tmtd (thiram), zineb (zineb), ziram (ziram), the mould prestige of second (diethofencarb), iprovalicarb (iprovalicarb), benzene metsulfovax (flubenthiavalicarb), hundred dimensions spirit (propamocarb), 3-(4-chlorphenyl)-3-(2-isopropoxycarbonylamino-3-methylbutyrylamino) methyl propionate,
With
F) other reactive compounds, as guanidine class: dodine (dodine), biguanide spicy acid salt (iminoctadine), guazatine (guazatine), Antibiotics: spring thunder element (kasugamycin), streptomycin (streptomycin), Polyoxin (polyoxins), jinggangmeisu (validamycinA), nitrophenyl derivative: binapacryl (binapacryl), karathane (dinocap), dinobuton (dinobuton), sulfur heterocyclic ring based compound: Delan (dithianon), Isoprothiolane (isoprothiolane), organo-metallic compound: triphenyltin salt, as fentinacetate (fentin-acetate), organic phosphorus compound: Hinosan (edifenphos), iprobenfos (iprobenfos), fosetyl (fosetyl), fosetyl aluminium (fosetyl-Aluminum), phosphorous acid and salt thereof, Ppyrazophos (pyrazophos), tolelofos-methyl (tolclofos-methyl), organochlorine compound: tpn (chlorothalonil), Euparen (dichlofluanid), flusulfamide (flusulfamide), hexachloro-benzene (hexachlorobenzene), Rabcide (phthalide), Pencycuron (pencycuron), pcnb (quintozene), thiophanate methyl (thiophanate-methyl), tolyfluanid (tolylfluanid), inorganic active compound: bordeaux mixture (Bordeaux mixture), Schweinfurt green, Kocide SD, Cupravit, basic copper sulfate, sulphur, other: cyflufenamid (cyflufenamid), cymoxanil (cymoxanil), Milcurb (dimethirimol), Milstem (ethirimol), Furalaxyl (furalaxyl), metrafenone (metrafenone) and spiral shell luxuriant amine (spiroxamine), growth retardant: adjust naphthenic acid (prohexadione) and salt, TrinexAN_SNacethyl (trinexapac-ethyl), chlormequat (chlormequat), help strong element (mepiquat-chloride) and difluoro pyrrole grand (diflufenzopyr).
In addition, the present invention relates to a kind of method, Compound I and reactive compound II using the mixture of Compound I and reactive compound II to prevent and treat harmful fungoid at the purposes prepared in such mixture and the composition comprising these mixtures.
Be called the azoles of the formula I of component 1 above and pyrimidin-7-ylamine, its preparation and to the effect of harmful fungoid by the known (EP-A71792 of document; EP-A141317; WO03/009687; WO05/087771; WO05/087772; WO05/087773; PCT/EP/05/002426; PCT/EP2006/050922; PCT/EP2006/060399).
As the above-mentioned reactive compound II of component 2, its preparation and to normally known (see the http://www.hclrss.demon.co.uk/index.html) of the effect of harmful fungoid; They can be commercial.Bitertanol, β-([1,1 '-biphenyl]-4-base oxygen base)-α-(1,1-dimethyl ethyl)-1H-1,2,4-triazole-1-ethanol (DE2324020);
Bromuconazole, 1-[[the bromo-2-of 4-(2,4-dichlorophenyl) tetrahydrochysene-2-furyl] methyl]-1H-[1,2,4]-triazole (Proc.1990Br.Crop.Prot.Conf.-PestsDis., the 1st volume, the 459th page);
Cyproconazole, 2-(4-chlorphenyl)-3-cyclopropyl-1-[1,2,4] triazol-1-yl fourth-2-alcohol (US4664696); ether azoles, 1-{2-[the chloro-4-of 2-(4-chlorophenoxy) phenyl]-4-methyl-[1,3] dioxolanes-2-ylmethyl }-1H-[1,2,4] triazole (GB-A2098607);
Olefin conversion, (β E)-β-[(2,4-dichlorophenyl) methylene]-α-(1,1-dimethyl ethyl)-1H-1,2,4-triazole-1-ethanol (NoyakuKagaku, the 1983,8th volume, the 575th page);
IMAZALIL (imazalil), 1-[2-(2,4-dichlorophenyl)-2-(2-propenyloxy group) ethyl]-1H-imidazoles (Fruits, the 1973,28th volume, the 545th page);
Oxole bacterium, (2RS, 3SR)-1-[3-(2-chlorphenyl)-2,3-epoxy-2-(4-fluorophenyl) propyl group]-1H-1,2,4-triazole (EP-A196038);
Fluquinconazole, 3-(2,4-dichlorophenyl)-6-fluoro-2-[1,2,4] triazol-1-yl-3H-quinazoline-4-one (Proc.Br.CropProt.Conf.-PestsDis., 5-3,411 (1992));
RH-7592, α-[2-(4-chlorphenyl) ethyl]-4-benzopyrone H-1,2,4-triazole-1-propionitrile (Proc.1988Br.CropProt.Conf.-PestsDis., the 1st volume, the 33rd page);
Flusilazole, 1-{ [two (4-fluorophenyl) methyl-monosilane base] methyl }-1H-[1,2,4] triazole (Proc.Br.CropProt.Conf.-PestsDis., Isosorbide-5-Nitrae 13 (1984));
Flutriafol, α-(2-fluorophenyl)-α-(4-fluorophenyl)-1H-1,2,4-triazole-1-ethanol (EP-A15756);
Own azoles alcohol, the own-2-alcohol (CASRN79983-71-4) of 2-(2,4-dichlorophenyl)-1-[1,2,4] triazol-1-yl;
Acid amides azoles, N-(2,4-dichlorophenyl)-1H-1,2,4-triazole-1-sulfo-ethanimidic acid (4-chlorphenyl) methyl ester ((Proc.1988Br.CropProt.Conf.-PestsDis., the 2nd volume, the 519th page),
Cycltebuconazole, 2-[(4-chlorphenyl) methyl]-5-(1-Methylethyl)-1-(1H-1,2,4-triazol-1-yl methyl) cyclopentanol (EP-A267778);
Ring penta azoles bacterium, 5-(4-chlorobenzyl)-2,2-dimethyl-1-[1,2,4] triazol-1-yl methylcyclopentanol (GB857383);
Nitrile bacterium azoles, 2-(4-chlorphenyl)-2-[1,2,4] triazol-1-yl methyl valeronitrile (CASRN88671-89-0);
Penconazole, 1-[2-(2,4-dichlorophenyl) amyl group]-1H-[1,2,4] triazole (PesticideManual, the 12nd edition (2000), the 712nd page);
Propiconazole, 1-[[2-(2,4-dichlorophenyl)-4-propyl group-DOX-2-base] methyl]-1H-1,2,4-triazole (BE835579);
Prothioconazoles, 2-[2-(1-chlorine cyclopropyl)-3-(2-chlorphenyl)-2-hydroxypropyl]-2,4-dihydros [1,2,4] triazole-3-thioketones (WO96/16048);
Simeconazoles, α-(4-fluorophenyl)-α-[(trimethyl silyl) methyl]-1H-1,2,4-triazole-1-ethanol [CASRN149508-90-7],
Triazolone, 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-2-butanone;
Triadimenol, β-(4-chlorophenoxy)-α-(1,1-dimethyl ethyl)-1H-1,2,4-triazole-1-ethanol;
Tebuconazole, 1-(4-chlorphenyl)-4,4-dimethyl-3-[1,2,4] triazol-1-yl methylpent-3-alcohol (EP-A40345);
Fluorine ether azoles, 1-[2-(2,4-dichlorophenyl)-3-(1,1,2,2-tetrafluoro ethyoxyl) propyl group]-1H-1,2,4-triazole (EP-A234242);
Triticonazole, (5E)-5-[(4-chlorphenyl) methylene]-2,2-dimethyl-1-(1H-1,2,4-triazol-1-yl methyl) cyclopentanol (FR2641277);
Prochloraz, N-{ propyl group-[2-(2,4,6-Trichlorophenoxy) ethyl] } imidazoles-1-formamide (US3991071);
Pefurazoate, 2-[(2-furyl methyl) (1H-imidazoles-1-base carbonyl) is amino] butyric acid 4-pentenyl ester [CASRN101903-30-4],
Fluorine bacterium azoles, (the chloro-2-trifluoromethyl of 4-)-(2-propoxyl group-1-[1,2,4] triazol-1-yl ethylidene) amine (JP-A79/119462);
Cyazofamid, the chloro-2-cyano group of 4--N, N-dimethyl-5-(4-aminomethyl phenyl)-1H-imidazoles-1-sulfonamide (CASRN120116-88-3);
Benomyl, N-butyl-2-acetylamino benzo imidazoles-1-formamide (US3631176);
Carbendazim, (1H-benzimidazolyl-2 radicals-Ji) methyl carbamate (US3657443);
Thiabendazole, 2-(1,3-thiazoles-4-base) benzimidazole (US3017415);
Furidazol, 2-(2-furyl)-1H-benzimidazole (DE-A1209799);
Guardian, N-(cyano group-2-thienyl methyl)-4-ethyl-2-(ethylamino)-5-thiazole carboxamides (EP-A639574);
Kobam,
Hydroxyisoxazole, 5-methyl isophthalic acid, 2- azoles-3-alcohol (JP518249, JP532202),
Nitrile Fluoxastrobin, 2-{2-[6-(2-cyano group-1-vinyl penta-1,3-diene oxygen base) pyrimidine-4-yl oxygen base] phenyl }-3-methoxy-methyl acrylate (EP-A382375),
Dimoxystrobin, (E)-2-(methoxyimino)-N-methyl-2-[α-(2,5-xylyloxy)-o-tolyl] acetamide (EP-A477631);
Fluoxastrobin, (E)-{ 2-[6-(2-chlorophenoxy)-5-FU-4-base oxygen base] phenyl } (5,6-dihydro-Isosorbide-5-Nitrae, 2-bis- piperazine-3-base) ketone O-methyloxime (WO97/27189);
Imines bacterium, (E)-methoxyimino [α-(oxy-o-cresyl)-o-tolyl] methyl acetate (EP-A253213);
Fork phenalgin acid amides, (E)-2-(methoxyimino)-N-methyl-2-(2-Phenoxyphenyl) acetamide (EP-A398692);
Orysastrobin, (2E)-2-(methoxyimino)-2-{2-[(3E, 5E, 6E)-5-(methoxyimino)-4,6-dimethyl-2,8-dioxa-3,7-diaza diene-1-in the ninth of the ten Heavenly Stems-3,6-base] phenyl }-N-methylacetamide (WO97/15552);
ZEN 90160,3-methoxyl group-2-[2-(6-5-flumethiazine-2-base oxygen ylmethyl) phenyl] methyl acrylate (EP-A278595);
Pyraclostrobin, N-{2-[1-(4-chlorphenyl)-1H-pyrazole-3-yl oxygen ylmethyl] phenyl } (N-methoxyl group) methyl carbamate (WO96/01256);
Oxime bacterium ester, (E)-methoxyimino-{ (E)-α-[1-(α, α, α-three fluoro-tolyls) ethyleneimino oxygen base]-o-tolyl } methyl acetate (EP-A460575);
Carboxin, 5,6-dihydro-2-Methyl-N-phenyl-Isosorbide-5-Nitrae-oxygen thiapyran-3-formamide (US3249499);
M 9834, N-(phenyl acetyl)-N-(2,6-xylyl)-DL-Alanine methyl esters (DE2903612);
Boscalid, the chloro-N-of 2-(4 '-chlordiphenyl-2-base) vitamin PP (EP-A545099);
Fenhexamid, N-(the chloro-4-hydroxy phenyl of 2,3-bis-)-1-hexahydrotoluene formamide (Proc.Br.CropProt.Conf.-PestsDis., the 1998,2nd volume, the 327th page);
Flutolanil, the fluoro-3 '-isopropoxy of α, α, α-three-adjacent toluyl aniline (JP1104514);
The spirit of furan pyrazoles, the chloro-N-of 5-(1,3-dihydro-1,1,3-trimethyl-4-isobenzofuran-base)-1,3-dimethyl-1H-pyrazole-4-carboxamide [CASRN123572-88-3];
Third oxygen goes out embroidery amine, 3 '-isopropoxy-adjacent toluyl aniline (US3937840);
Metalaxyl, N-(Methoxyacetyl)-N-(2,6-xylyl)-DL-Alanine methyl esters (GB1500581);
Metalaxyl-M, N-(2,6-xylyl)-N-(Methoxyacetyl)-D-alanine methyl esters;
Fenfuram, (RS)-α-(2-chloro-N-2,6-xylyl acetamido)-gamma-butyrolacton [CASRN58810-48-3];
frost spirit, N-(2,6-3,5-dimethylphenyl)-2-methoxyl group-N-(2-oxo-3- oxazolidinyl) acetamide (GB2058059);
Oxycarboxin, 5,6-dihydro-2-methyl isophthalic acid, 4-oxygen thiapyran-3-formailide 4,4-dioxide (US3399214);
Pyrrole metsulfovax, N-[2-(1,3-dimethylbutyl)-3-thienyl]-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide (JP10/130268);
Thifluzamide, N-[the bromo-4-of 2,6-bis-(trifluoromethoxy) phenyl]-2-methyl-4-(trifluoromethyl)-5-thiazole carboxamides;
Tiadinil, 3 '-chloro-4,4 '-dimethyl-1,2,3-thiadiazoles-5-formailide [CASRN223580-51-6];
Dimethomorph, 3-(4-chlorphenyl)-3-(3,4-Dimethoxyphenyl)-1-morpholine-4-base propenone (EP-A120321);
Flumorph, 3-(4-fluorophenyl)-3-(3,4-Dimethoxyphenyl)-1-morpholine-4-base propenone (EP-A860438);
Fluorine biphenyl bacterium, 2-(3,4-Dimethoxyphenyl)-N-ethyl-α, α, α-trifluoro-N-methyl is to toluamide [AGROWNo.243,22 (1995)];
Fluopicolide (picobenzamid), the chloro-N-of 2,6-bis-(3-chloro-5-trifluoromethylpyridine-2-ylmethyl) benzamide (WO99/42447);
Zoxamide, (RS)-3,5-bis-chloro-N-(the chloro-1-ethyl of 3--1-methyl-2-oxopropyl)-to toluamide [CASRN156052-68-5];
Carpropamide, the chloro-N-of 2,2-bis-[1-(4-chlorphenyl) ethyl]-1-ethyl-3-methylcyclopropanecarboxamide [CASRN104030-54-8];
Two chlorine zarilamid, 2-cyano group-N-[(1R)-1-(2,4-dichlorophenyl) ethyl]-3,3-amide dimethyl butyrates;
Mandipropamid, (RS)-2-(4-chlorphenyl)-N-[3-methoxyl group-4-(Propargyl oxygen base) phenethyl]-2-(Propargyl oxygen base) acetamide [CASRN374726-62-2];
Fluazinam, the chloro-N-of 3-[3-chloro-2,6-dinitro-4-(trifluoromethyl) phenyl]-5-(trifluoromethyl)-2-pyridine amine (ThePesticideManual, publ.TheBritishCropProtectionCouncil, 10th edition (1995), the 474th page);
Pyrifenox, 1-(2,4-dichlorophenyl)-2-(3-pyridine radicals) ethyl ketone O-methyloxime (EP-A49854);
The phonetic bacterium spirit of sulphur, sulfamic acid 5-butyl-2-ethylamino-6-methylpyrimidine-4-base dimethyl esters [CASRN41483-43-6];
Ring third pyrimidine, (4-cyclopropyl-6-methylpyrimidine-2-base) phenyl amine (EP-A310550);
Fenarimol, (4-chlorphenyl) (2-chlorphenyl) pyrimidine-5-base methyl alcohol (GB1218623);
Ferimzone, (Z)-2 '-methyl acetophenone-4,6-dimethyl pyrimidine-2-base hydrazone [CASRN89269-64-7];
Mepanipyrim, (4-methyl-6-third-1-acetylenic-2-base) phenyl amine (EP-A224339);
Nuarimol, α-(2-chlorphenyl)-α-(4-fluorophenyl)-5-rubigan (GB1218623);
Pyrimethanil, 4,6-dimethyl pyrimidine-2-base phenyl amine (DD-A151404);
Triforine, N, N '-{ piperazine-Isosorbide-5-Nitrae-two base two [(trichloromethyl) methylene] } diformamide (DE1901421);
Fenpiclonil, 4-(2,3-dichlorophenyl)-1H-pyrroles-3-formonitrile HCN (Proc.1988Br.CropProt.Conf.-PestsDis., the 1st volume, the 65th page);
Fluorine bacterium, 4-(2,2-difluoro benzo [1,3] Dioxol-4-yl)-1H-pyrroles-3-formonitrile HCN (ThePesticideManual, publ.TheBritishCropProtectionCouncil, the 10th edition (1995), the 482nd page);
4-dodecyl-2,6-thebaine, comprise 65-75%2, the 4-alkyl-2,5 of 6-thebaine and 25-35%2,5-thebaine (or 2,6)-thebaine, wherein be 4-dodecyl-2,5 (or 2,6)-thebaine more than 85% and wherein " alkyl " also comprise octyl group, decyl, myristyl and cetyl and wherein cis/trans ratio be 1:1;
Dodemorfe, 4-cyclo-dodecyl-2,6-thebaine (DE1198125);
Butadiene morpholine, (RS)-cis-4-[3-(4-tert-butyl-phenyl)-2-methyl-propyl]-2,6-thebaines (DE2752096);
Tridemorph, 2,6-dimethyl-4-tridecyl morpholine (DE1164152);
Fenpropidin, (RS)-1-[3-(4-tert-butyl-phenyl)-2-methyl-propyl] piperidines (DE2752096);
Isopropyl is fixed, N-isopropyl-3-(3,5-dichlorophenyl)-2,4-dioxo alkyl imidazole-1-formamide (GB1312536);
Sterilization profit, N-(3,5-dichlorophenyl)-1,2-dimethylcyclopropane-1,2-dicarboximide (US3903090);
Vinclozolin, 3-(3,5-dichlorophenyl)-5-methyl-5-vinyl azoles alkane-2,4-diketone (DE-OS2207576);
famoxadone, (RS)-3-anilino--5-methyl-5-(4-Phenoxyphenyl)-1,3- azoles alkane-2,4-diketone;
Fenamidone, (S)-1-anilino--4-methyl-2-methyl mercapto-4-benzylimidazoline-5-ketone;
Different thiophene bacterium ketone,
Probenazole, 3-allyloxy-1,2-[4-morpholinodithio 1,1-dioxide;
Amisulbrom, N, N-dimethyl-3-(the fluoro-2 methyl indole of the bromo-6-of 3--1-sulfonyl)-[1,2,4] triazole-1-sulfonamide (WO03/053145);
Anilazine, the chloro-N-of 4,6-bis-(2-chlorphenyl)-1,3,5-triazines-2-amine (US2720480);
Diclomezine, 6-(3,5-dichlorophenyl)-p-methylphenyl) pyridazine-3 (2H)-one;
Pyroquilon,
Third oxygen quinoline, the iodo-2-propoxyl group of 6--3-propyl group quinazoline-4 (3H)-one (WO97/48684);
Tricyclazole, 5-methyl isophthalic acid, 2,4-triazol [3,4-b] benzothiazole (GB1419121);
Thiadiazoles element, benzo [1,2,3] thiadiazoles-7-carbithionic acid methyl ester;
Difoltan, N-(1,1,2,2-tetrachloro ethylmercapto group) hexamethylene-4-alkene-1,2-dicarboximide;
Captan, 2-trichloro-methylthio-3a, 4,7,7a-tetrahydrochysene benzazine-1,3-diketone (US2553770);
Dazomet, 3,5-dimethyl-1,3,5-thiadiazine alkane-2-thioketones;
Folpet, 2-trichloro-methylthio benzazine-1,3-diketone (US2553770);
Zarilamid, N-(1-cyano group-1,2-dimethyl propyl)-2-(2,4-dichlorophenoxy) propionamide;
Quinoxyfen, the chloro-4-of 5,7-bis-(4-fluorophenoxy) quinoline (US5240940);
Mancozeb, ethylene (aminodithioformic acid) MnZn complex (US3379610);
Maneb, ethylene (aminodithioformic acid) manganese (US2504404);
Metham-sodium, methyl aminodithioformic acid (US2791605);
Carbatene, ethylene (aminodithioformic acid) zinc ammonate (US3248400);
Propineb, propylidene two (aminodithioformic acid) zinc complex (BE611960);
Ferbam, ferric dimethyl dithiocarbamate (3+) (US1972961);
Tmtd, two (dimethylthiocarbamoyl) disulphide (DE642532);
Ziram, aminodithioformic acid dimethyl esters;
Zineb, ethylene (aminodithioformic acid) zinc (US2457674);
The mould prestige of second, 3,4-diethoxybenzene amido formic acid isopropyl esters;
Iprovalicarb, [(1S)-2-methyl isophthalic acid-(1-p-methylphenyl ethylaminocarbonyl) propyl group] carbamic acid isopropyl ester (EP-A472996);
Benzene metsulfovax (benthiavalicarb), { (S)-1-[(1R)-1-(6-fluoro benzothiazole-2-base) ethylaminocarbonyl]-2-methyl-propyl } carbamic acid isopropyl esters (JP-A09/323984);
Hundred dimension spirits, 3-(dimethylamino) propyl carbamic acid propyl diester (DE1643040);
Dodine, (2,4-dichlorophenoxy) acetic acid (US2867562);
Biguanide spicy acid salt, two (8-guanidine radicals octyl group) amine (GB1114155);
Guazatine, the product mixtures formed by the amidatioon of imino-diacetic (eight methylene) diamines, mainly biguanide spicy acid salt;
Spring thunder element, the Arabic pyranohexose of amino-2,3,4,6-tetra-deoxidation-4-(the alpha-imino glycyl)-α-D-of 1L-1,3,4/2,5,6-1-deoxidation-2,3,4,5,6-penta hydroxy group cyclohexyl 2-;
Streptomycin, O-2-deoxidation-2-methylamino-α-L-glycopyranosyl-(1 → 2)-O-5-deoxidation-3-C-formoxyl-α-L-furans lysol glycosyl-(1 → 4) N 1, N 3-diamidino-D-streptamine;
Polyoxin, 5-(2-amino-5-O-carbamoyl-2-deoxidation-L-xylonamide base)-1-(5-carboxyl-1,2,3,4-tetrahydrochysene-2,4-dioxo pyrimidine-1-base)-1,5-dideoxy-β-D-allofuranose aldehydic acid and salt thereof; Jinggangmeisu,
Binapacryl, 3-methylcrotonic acid (RS)-2-sec-butyl-4,6-dinitrophenyl ester;
Karathane, the mixture of crotonic acid 2,6-dinitro-4-octyl phenyl ester and crotonic acid 2,4-dinitro-6-octyl phenyl ester, wherein " octyl group " be 1-methylheptyl, the mixture (US2526660) of 1-ethylhexyl and 1-propylpentyl;
Dinobuton, carbonic acid (RS)-2-sec-butyl-4,6-dinitrophenyl isopropyl esters;
Delan, 5,10-dioxo-5,10-dihydro-naphtho [2,3-b] [Isosorbide-5-Nitrae] two thiophene English-2,3-dimethoxy nitrile (GB857383);
Isoprothiolane, indol-3-yl acetic acid;
Fentinacetate, fentinacetate (US3499086);
Hinosan, phosphonodithioic acid O-ethyl S, S-diphenyl;
Iprobenfos, phosphonothiolic acid S-benzyl O, O-diisopropyl ester (Jpn.PesticideInf., the 2nd phase, the 11st page (1970));
Fosetyl, fosetyl aluminium, phosphinic acid ethyl ester (aluminium) (FR2254276);
Ppyrazophos, 2-diethoxy sulfo-phosphonato-5-methylpyrazole also [1,5-a] pyrimidine-6-Ethyl formate (DE1545790);
Tolelofos-methyl, phosphonothiolic acid O-2,6-dichloro-p-toluene base O, O-dimethyl esters (GB1467561);
Tpn, 2,4,5,6-termil (US3290353);
Euparen, N-dichloro one fluorine methyl mercapto-N ', N '-dimethyl-N-phenyl-sulfamide (DE1193498);
Flusulfamide, toluol sulfonanilide (EP-A199433) between 2 ', 4-bis-chloro-α, α, α-three fluoro-4 '-nitro;
Hexachloro-benzene (C.R.SeancesAcad.Agric.Fr., the 31st volume, the 24th page (1945));
Rabcide (DE1643347);
Pencycuron, 1-(4-chlorobenzyl)-1-cyclopenta-3-phenylurea (DE2732257);
Pcnb, pentachloro-nitrobenzene (DE682048);
Thiophanate methyl, 1,2-phenylene two (imino group thiocarbonyl) two (carbamic acid methyl ester) (DE-OS1930540);
Tolyfluanid, N-dichloro one fluorine methyl mercapto-N, N-dimethyl-N-p-methylphenyl sulfonamide (DE1193498);
Bordeaux mixture, the mixture of slaked lime and copper sulphate (II);
Kocide SD, Cu (OH) 2; Cupravit, Cu 2cl (OH) 3;
Cyflufenamid, (Z)-N-[α-(cyclopropyl-methoxy imino group)-2,3-bis-fluoro-6-(trifluoromethyl) benzyl]-2-phenyl-acetamides (WO96/19442);
Cymoxanil, 1-(2-cyano group-2-methoxyimino acetyl group)-3-ethyl carbamide (US3957847);
Milcurb, 5-butyl-2-dimethylamino-6-methylpyrimidine-4-alcohol (GB1182584);
Milstem, 5-butyl-2-ethylamino-6-methylpyrimidine-4-alcohol (GB1182584);
Furalaxyl, N-(2-furoyl base)-N-(2,6-xylyl)-DL-Alanine methyl esters (GB1448810);
Metrafenone, 3 '-bromo-2,3,4,6 '-tetramethoxy-2 ', 6-dimethyl acetophenone (US5945567);
Spiral shell luxuriant amine, (the 8-tert-butyl group-Isosorbide-5-Nitrae-dioxo spiro [4.5]-2-in last of the ten Heavenly stems base) diethylamide (EP-A281842).
According to IUPAC name compound, its preparation and fungicidal action be known equally:
(the chloro-5-of 2-[1-(3-methylbenzyloxy imino group) ethyl] benzyl) methyl carbamate, (the chloro-5-of 2-[1-(6-picoline-2-base methoxyimino) ethyl] benzyl) methyl carbamate (EP-A1201648);
2-(o-((2,5-dimethylphenyloxymethylene) phenyl)-3-methoxy-methyl acrylate (EP-A226917);
The chloro-7-of 5-(4-methyl piperidine-1-base)-6-(2,4,6-trifluorophenyl)-[1,2,4] triazol [1,5-a] pyrimidine (WO98/46608),
The chloro-N-of 3,4-bis-(2-cyano-phenyl) isothiazole-5-formamide (WO99/24413),
N-(2-{4-[3-(4-chlorphenyl) third-2-alkynyloxy group]-3-anisyl } ethyl)-2-methanesulfonamido-3-methylbutyryl amine, N-(2-{4-[3-(4-chlorphenyl) third-2-alkynyloxy group]-3-anisyl } ethyl)-2-second sulfonamido-3-methylbutyryl amine (WO04/049804)
N-(4 '-bromo biphenyl-2-base)-4-difluoromethyl-2-methylthiazol-5-formamide, N-(4 '-trifluoromethyl-biphenyl-2-base)-4-difluoromethyl-2-methylthiazol-5-formamide, N-(4 '-chloro-3 '-fluorine biphenyl-2-base)-4-difluoromethyl-2-methylthiazol-5-formamide, N-(3 ', 4 '-two chloro-4-fluorine biphenyl-2-base)-3-difluoromethyl-1-methylpyrazole-4-formamide (WO03/066609), N-(3', 4'-bis-chloro-5-fluorine biphenyl-2-base)-3-difluoromethyl-1-methylpyrazole-4-formamide (WO03/053145);
2-butoxy-6-iodo-3-propyl group chromene-4-ketone (WO03/14103),
[5-(4-chlorphenyl)-2,3-dimethyl are different for 3- azoles alkane-3-base] pyridine (EP-A1035122);
Amisulbrom, N, N-dimethyl-3-(the fluoro-2 methyl indole of the bromo-6-of 3--1-sulfonyl)-[1,2,4] triazole-1-sulfonamide (WO03/053145);
3-(4-chlorphenyl)-3-(2-isopropoxycarbonylamino-3-methylbutyrylamino) methyl propionate (EP-A1028125).
In order to reduce the rate of application of known compound and widen its activity profile, the object of this invention is to provide to harmful fungoid under total amount of application of reactive compound reduces, especially some indication is had and improve active mixture.
We find that this object realizes by starting defined mixture.In addition, we find compared with single compound, meanwhile, namely associating or separate administration Compound I and reactive compound II or successively administered compound I and reactive compound II can prevent and treat harmful fungoid (Synergistic mixture) better.
Compound I can be used as the synergetic effect additive of a large amount of different Fungicidal active compound.Meanwhile, namely associating or separate administration Compound I and reactive compound II super add and add Fungicidally active.
The mixture of Compound I and reactive compound II, or simultaneously, namely combine or separately use Compound I and reactive compound II to the plant pathogenic fungi of wide region, the fungi being especially selected from Ascomycetes (Ascomycetes), deuteromycetes (Deuteromycetes), Oomycete (Oomycetes) and Basidiomycetes (Basidiomycetes) has excellent activity.Inhale effective in some in them and can be used in crop protection as blade face fungicide, seed dressing fungicide and soil fungicide.
They are even more important to preventing and treating a large amount of fungi in various crop plant is as banana, cotton, vegetables (as cucumber, beans and cucurbitaceous plant), barley, dogstail, oat, coffee, potato, corn, fruit, rice, rye, soybean, tomato, grape vine, wheat, ornamental plants, sugarcane and multiple seed.
They are advantageously applicable to preventing and treating following plants disease:
● the Alternaria (Alternaria) on vegetables, oilseed rape, sugar beet, fruit and rice, such as, early epidemic rod method (A.solani) on potato and tomato or rod method (A.alternata);
● the Aphanomyces (Aphanomyces) on sugar beet and vegetables;
● the Ascochyta (Ascochyta) on Cereal and vegetables;
● the Bipolaris (Bipolaris) in corn, Cereal, rice and lawn and Drechslera (Drechslera), such as, Bipolaris maydis (D.maydis) on corn;
● standing grain powdery mildew (Blumeriagraminis) (powdery mildew) on Cereal;
● Botrytis cinerea (Botrytiscinerea) (gray mold) on strawberry, vegetables, flowers and grape vine,
● lettuce dish stalk mould (Bremialactucae) on lettuce,
● the Cercospora (Cercospora) on corn, soybean, rice and sugar beet;
● the cochliobolus on corn, Cereal, rice belongs to (Cochliobolus), such as, standing grain cochliobolus (Cochliobolussativus) on Cereal, palace portion cochliobolus (Cochliobolusmiyabeanus) on rice;
● the perverse dish spore on soybean and cotton belongs to (Colletotricum);
● the Drechslera (Drechslera) on corn, Cereal, rice and lawn, nuclear cavity Pseudomonas (Pyrenophora), the D.tritci-repentis in such as, barley filigree on barley on the compacted spore of navel (D.teres) or wheat;
● the Eschka (Esca) on the grape vine caused by Phaeoacremoniumchlamydosporium, Ph.Aleophilum and Formitiporapunctata (synonym spot hole Phellinus (Phellinuspunctatus));
● the prominent navel Helminthosporium (Exserohilum) on corn,
● two spore powdery mildews (Erysiphecichoracearum) on cucumber and monofilament shell powdery mildew (Sphaerothecafuliginea),
● the Fusarium (Fusarium) on each Plants and Verticillium (Verticillium), such as, fusarium graminaria (F.graminearum) on Cereal or machete sickle spore (F.culmorum) or various plants are as the sharp sickle spore (F.oxysporum) on tomato;
● the gaeumannomyce (Gaeumanomycesgraminis) on Cereal;
● the Gibberella (Gibberella) (gibberella fujikuroi (Gibberellafujikuroi) on such as rice) on Cereal and rice;
● the Grainstainingcomplex on rice;
● the Helminthosporium (Helminthosporium) on corn and rice;
● the Michrodochiumnivale on Cereal;
● the mycosphaerella (Mycosphaerella) on Cereal, banana and peanut, Fijian ball chamber bacterium (M.fijiensis) on such as, standing grain green-ball chamber bacterium (M.graminicola) on wheat or banana;
● the Peronospora (Peronospora) on cabbage and plant bulbs, such as, rape downy mildew (P.brassicae) on cabbage or the shallot downy mildew (P.destructor) on onion;
● the Phakopsora pachyrhizi (Phakopsorapachyrhizi) on soybean and mountain horseleech layer rest fungus (Phakopsarameibomiae);
● the Phomopsis (Phomopsis) on soybean and sunflower;
● the phytophthora infestans (Phytophthorainfestans) on potato and tomato;
● the Phytophthora (Phytophthora) on each Plants, such as, Phytophthora capsici (P.capsici) on green pepper;
● the raw single shaft of the grape on grape vine mould (Plasmoparaviticola),
● the apple mildew bacterium (Podosphaeraleucotricha) on apple,
● the wheat Phyllostachys pubescens (Pseudocercosporellaherpotrichoides) on Cereal,
● the Pseudoperonospora (Pseudoperonospora) on each Plants, such as, Pseudoperonospora cubensis (P.Cubensis) on cucumber or the false frost (P.Humili) of the grass of the humulus on lupulus;
● the Puccinia (Puccinia) on each Plants, such as, wheat handle rest fungus (P.triticina) on Cereal, bar shaped handle rust (P.striformis), barley handle rust (P.hordei) or puccinia graminis (P.graminis), or the Asparagus handle rust (P.asparagi) on asparagus);
● Pyricularia oryzae (Pyriculariaoryzae), Bamboo grass wood photovoltaicing leather bacteria (Corticiumsasakii), broom stalk Cylindrocarpon (Sarocladiumoryzae), sheath rot of rice plant (S.attenuatum), rice leaf smut (Entylomaoryzae) on rice
● the piricularia oryzae (Pyriculariagrisea) on lawn and Cereal,
● the pythium (Pythium) on lawn, rice, corn, cotton, oilseed rape, sunflower, sugar beet, vegetables and other plant, such as, Pythium ultimum bacterium (P.ultiumum) on each Plants, the melon and fruit corruption on lawn is mould (P.aphanidermatum);
● the Rhizoctonia (Rhizoctonia) on cotton, rice, potato, lawn, corn, oilseed rape, sugar beet, vegetables and each Plants, such as, miliary damping-off germ (R.solani) on beet and each Plants;
● the rye beak spore (Rhynchosporiumsecalis) on barley, rye and triticale;
● the Sclerotinia (Sclerotinia) on oilseed rape and sunflower;
● the wheat septoria (Septoriatritici) on wheat and the many spores of the withered shell of grain husk (Stagonosporanodorum),
● the grape snag shell (Erysiphe (synonym Uncinula) necator) on grape vine,
● the Setospaeria on corn and lawn belongs to,
● the silk axle smut (Sphacelothecareilinia) on corn,
● the Thiclaviopsis (Thievaliopsis) on soybean and cotton,
● the Tilletia (Tilletia) on Cereal,
● the Ustilago (Ustilago) on Cereal, corn and sugarcane, such as, Ustilago maydis (U.maydis) on corn;
● Venturia (Venturia) (scab) on apple and pears, such as, apple scab (V.inaequalis) on apple.
The mixture of Compound I and reactive compound II is particularly suitable for control and is selected from Peronosporomycetes (synonym: Oomycete), the harmful fungoid of as mould in Peronospora, Phytophthora, the raw single shaft of grape and Pseudoperonospora, especially corresponds to those fungi above-mentioned.
Compound I and reactive compound II can simultaneously, i.e. associating or separate administration, or use successively, when separate administration, order of administration usually on the result of prophylactico-therapeutic measures without any impact.
To above formula give in the definition of symbol, use the collective term usually representing substituents:
Halogen: fluorine, chlorine, bromine and iodine;
Alkyl: saturated straight chain or the branched hydrocarbyl radical with 1-4,1-6,1-8 or 1-10 carbon atom, such as C 1-C 6alkyl, as methyl, ethyl, propyl group, 1-Methylethyl, butyl, 1-methyl-propyl, 2-methyl-propyl, 1, 1-dimethyl ethyl, amyl group, 1-methyl butyl, 2-methyl butyl, 3-methyl butyl, 2, 2-dimethyl propyl, 1-ethyl propyl, hexyl, 1, 1-dimethyl propyl, 1, 2-dimethyl propyl, 1-methyl amyl, 2-methyl amyl, 3-methyl amyl, 4-methyl amyl, 1, 1-dimethylbutyl, 1, 2-dimethylbutyl, 1, 3-dimethylbutyl, 2, 2-dimethylbutyl, 2, 3-dimethylbutyl, 3, 3-dimethylbutyl, 1-ethyl-butyl, 2-ethyl-butyl, 1, 1, 2-thmethylpropyl, 1, 2, 2-thmethylpropyl, 1-ethyl-1-methyl-propyl and 1-Ethyl-2-Methyl propyl group,
Haloalkyl: straight chain or the branched-alkyl (as mentioned above) with 1-2,1-4 or 1-6 carbon atom, the some or all hydrogen atoms wherein in these groups can be replaced by above-mentioned halogen atom: especially C 1-C 2haloalkyl, as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, methyl fluoride, difluoromethyl, trifluoromethyl, chlorine methyl fluoride, dichloro one methyl fluoride, a chlorodifluoramethyl-, 1-chloroethyl, 1-bromoethyl, 1-fluoro ethyl, 2-fluoro ethyl, 2,2-bis-fluoro ethyl, 2,2,2-trifluoroethyls, 2-chloro-2-fluoro ethyl, 2-chloro-2,2-bis-fluoro ethyl, 2, the chloro-2-fluoro ethyl of 2-bis-, 2,2,2-trichloroethyl, pentafluoroethyl group or 1,1,1-trifluoropropyl-2-base.
Consider the azoles of formula I and the intended use of pyrimidine radicals amine, particularly preferably substituent following meanings, in each case alone or in combination:
Specially suitable to inventive mixture is wherein R 1for can by 1-3 halogen or C 1-C 4the straight chain that alkyl replaces or branching C 3-C 12the formula I of alkyl or phenyl.
In an embodiment of formula I, radicals R ado not exist.
Preferred embodiment relates to wherein R 1for straight chain or branching C 5-C 10the formula I of alkyl, especially ethyl, 3,5,5-trimethyl, n-heptyl, n-octyl, n-nonyl and positive decyl.
Another embodiment relates to as shown in the formula I, wherein R 1for phenyl, this phenyl is not substituted or by 1-4 halogen, cyano group, hydroxyl, sulfydryl, nitro, NR ar b, C 1-C 10alkyl, C 1-C 6haloalkyl, C 2-C 6alkenyl, C 2-C 6alkynyl and C 1-C 6alkoxyl replaces.
Preferred formula I is wherein R 1those of phenyl are substituted for what correspond to group G:
Wherein
L 1for cyano group, halogen, hydroxyl, sulfydryl, nitro, NR ar b, C 1-C 10alkyl, C 1-C 6halo
Alkyl, C 2-C 6alkenyl, C 2-C 6alkynyl and C 1-C 6alkoxyl; And
L 2, L 3be hydrogen or at L independently of each other 1under one of the group mentioned, and
# represents with azoles and the key that is connected of pyrimidine scaffold.
In another embodiment of formula I, L 1for cyano group, halogen, hydroxyl, sulfydryl, nitro, NR ar b, C 1-C 6alkyl, halogenated methyl or C 1-C 2alkoxyl, preferred cyano group, halogen, C 1-C 6alkyl, halogenated methyl or C 1-C 2alkoxyl.
In another embodiment of formula I, L 2for one of hydrogen or above-mentioned group.
In another embodiment of formula I, L 3for hydrogen, cyano group, halogen, hydroxyl, sulfydryl, nitro, NR ar b, C 1-C 6alkyl, halogenated methyl or C 1-C 2alkoxyl, preferred hydrogen.
Preferred wherein R 2for straight chain or branching C 1-C 12alkyl, C 1-C 4alkoxy-C 1-C 4alkyl or C 1-C 4the formula I of haloalkyl.
In the particularly preferred embodiment of formula I, R 2for methyl, ethyl, n-pro-pyl, n-octyl, trifluoromethyl or methoxyl methyl, especially methyl, ethyl, trifluoromethyl or methoxyl methyl.
Preferred wherein R in addition 3for the formula I of hydrogen.
In another embodiment of formula I, R 3for amino.
It is those of N that an embodiment of formula I relates to wherein A.These compounds correspond to wherein each variable as to formula I the formula IA that defines:
It is those of CH that another embodiment of formula I relates to wherein A.These compounds correspond to wherein each variable as to formula I the formula IB that defines:
In other embodiments of preferred compound I, R 1and R 2carbochain do not have together more than 12 carbon atoms.
Consider the application of Compound I, especially preferably compilation Compound I in the following table.In addition, the group that in his-and-hers watches, substituting group is mentioned, originally as described substituent particularly preferred embodiment, has nothing to do with the combination wherein mentioning them.
Table 1
Wherein R 1, R 2and R 3combination compound is corresponded in each case to the formula IA compound of a line of Table I
Table 2
Wherein R 1, R 2and R 3combination compound is corresponded in each case to the formula IB compound of a line of Table I
Table I
The preferred embodiment of inventive mixture comprises and is selected from following compound as active component 1:6-(3, 4-dichlorophenyl)-5-methyl-[1, 2, 4] triazol [1, 5-a] pyrimidin-7-ylamine, 6-(4-tert-butyl-phenyl)-5-methyl-[1, 2, 4] triazol [1, 5-a] pyrimidin-7-ylamine, 5-methyl-6-(3, 5, 5-trimethyl)-[1, 2, 4] triazol [1, 5-a] pyrimidin-7-ylamine, 5-methyl-6-octyl group-[1, 2, 4] triazol [1, 5-a] pyrimidin-7-ylamine, 5-ethyl-6-octyl group-[1, 2, 4] triazol [1, 5-a] pyrimidine-2, 7-diamines, 6-ethyl-5-octyl group-[1, 2, 4] triazol [1, 5-a] pyrimidin-7-ylamine, 5-ethyl-6-octyl group-[1, 2, 4] triazol [1, 5-a] pyrimidin-7-ylamine, 5-ethyl-6-(3, 5, 5-trimethyl)-[1, 2, 4] triazol [1, 5-a] pyrimidin-7-ylamine, 6-octyl group-5-propyl group-[1, 2, 4] triazol [1, 5-a] pyrimidin-7-ylamine, 5-methoxyl methyl-6-octyl group-[1, 2, 4] triazol [1, 5-a] pyrimidin-7-ylamine, 6-octyl group-5-trifluoromethyl-[1, 2, 4] triazol [1, 5-a] pyrimidin-7-ylamine and 5-trifluoromethyl-6-(3, 5, 5-trimethyl)-[1, 2, 4] triazol [1, 5-a] pyrimidin-7-ylamine.
Other preferred embodiments of inventive mixture relate to the compound of table 1, the combination of one of preferred compound I especially and one of following reactive compound II:
A) azole, as cyproconazole, ether azoles, Fluquinconazole, Flusilazole, ring penta azoles bacterium, propiconazole, prothioconazoles, Tebuconazole, Prochloraz, cyazofamid, carbendazim, Guardian;
B) strobilurins class, as nitrile Fluoxastrobin, Enestroburin, fluoxastrobin, pyraclostrobin, oxime bacterium ester or (the chloro-5-of 2-[1-(3-methyl-benzyloxyimino) ethyl] benzyl) methyl carbamate [B-6], (the chloro-5-of 2-[1-(6-picoline-2-base methoxyimino) ethyl] benzyl) methyl carbamate [B-7];
C) carboxyl acylamide, as M 9834, Boscalid, metalaxyl, fenfuram, frost spirit, dimethomorph, fluopicolide (picobenzamid), zoxamide, mandipropamid;
D) heterocyclic compound, as fixed in fluazinam, ring third pyrimidine, pyrimethanil, dodemorfe, isopropyl, vinclozolin, the chloro-7-of famoxadone, Fenamidone, amisulbrom, 5-(4-methyl piperidine-1-base)-6-(2,4,6-trifluorophenyl)-[1,2,4] triazol [1,5-a] pyrimidine [D-8], captan, folpet;
E) Carbamates, as mancozeb, maneb, Carbatene, propineb, iprovalicarb, benzene metsulfovax, 3-(4-chlorphenyl)-3-(2-isopropoxycarbonylamino-3-methylbutyrylamino) methyl propionate [E-7]; With
F) other reactive compounds, are selected from sulfur heterocyclic ring based compound: Delan; Organic phosphorus compound: fosetyl, fosetyl aluminium, phosphorous acid and salt thereof; Organochlorine compound: tpn, thiophanate methyl; Inorganic active compound: bordeaux mixture, Schweinfurt green, Kocide SD, Cupravit, basic copper sulfate; Other: cymoxanil, metrafenone; Growth retardant: adjust naphthenic acid and salt thereof.
Preferred embodiment relates to listed composition in Table A, wherein a line of Table A is corresponding to a kind of Fungicidal composition of reactive compound comprising mentioned specific formula I (component 1) and above-mentioned group in each case, and wherein this reactive compound is preferably selected from preferred embodiment as defined above.
Table A
OK Component 1 Component 2
A-1 Table 1, I-9 A group reactive compound II
A-2 Table 1, I-9 B group reactive compound II
OK Component 1 Component 2
A-3 Table 1, I-9 C group reactive compound II
A-4 Table 1, I-9 D group reactive compound II
A-5 Table 1, I-9 E group reactive compound II
A-6 Table 1, I-9 F group reactive compound II
A-7 Table 1, I-18 A group reactive compound II
A-8 Table 1, I-18 B group reactive compound II
A-9 Table 1, I-18 C group reactive compound II
A-10 Table 1, I-18 D group reactive compound II
A-11 Table 1, I-18 E group reactive compound II
A-12 Table 1, I-18 F group reactive compound II
A-13 Table 1, I-25 A group reactive compound II
A-14 Table 1, I-25 B group reactive compound II
A-15 Table 1, I-25 C group reactive compound II
A-16 Table 1, I-25 D group reactive compound II
A-17 Table 1, I-25 E group reactive compound II
A-18 Table 1, I-25 F group reactive compound II
A-19 Table 1, I-28 A group reactive compound II
A-20 Table 1, I-28 B group reactive compound II
A-21 Table 1, I-28 C group reactive compound II
A-22 Table 1, I-28 D group reactive compound II
A-23 Table 1, I-28 E group reactive compound II
A-24 Table 1, I-28 F group reactive compound II
A-25 Table 1, I-98 A group reactive compound II
A-26 Table 1, I-98 B group reactive compound II
A-27 Table 1, I-98 C group reactive compound II
A-28 Table 1, I-98 D group reactive compound II
A-29 Table 1, I-98 E group reactive compound II
A-30 Table 1, I-98 F group reactive compound II
A-31 Table 1, I-101 A group reactive compound II
A-32 Table 1, I-101 B group reactive compound II
A-33 Table 1, I-101 C group reactive compound II
A-34 Table 1, I-101 D group reactive compound II
A-35 Table 1, I-101 E group reactive compound II
A-36 Table 1, I-101 F group reactive compound II
A-37 Table 1, I-110 A group reactive compound II
A-38 Table 1, I-110 B group reactive compound II
OK Component 1 Component 2
A-39 Table 1, I-110 C group reactive compound II
A-40 Table 1, I-110 D group reactive compound II
A-41 Table 1, I-110 E group reactive compound II
A-42 Table 1, I-110 F group reactive compound II
A-43 Table 1, I-113 A group reactive compound II
A-44 Table 1, I-113 B group reactive compound II
A-45 Table 1, I-113 C group reactive compound II
A-46 Table 1, I-113 D group reactive compound II
A-47 Table 1, I-113 E group reactive compound II
A-48 Table 1, I-113 F group reactive compound II
A-49 Table 1, I-120 A group reactive compound II
A-50 Table 1, I-120 B group reactive compound II
A-51 Table 1, I-120 C group reactive compound II
A-52 Table 1, I-120 D group reactive compound II
A-53 Table 1, I-120 E group reactive compound II
A-54 Table 1, I-120 F group reactive compound II
A-55 Table 1, I-180 A group reactive compound II
A-56 Table 1, I-180 B group reactive compound II
A-57 Table 1, I-180 C group reactive compound II
A-58 Table 1, I-180 D group reactive compound II
A-59 Table 1, I-180 E group reactive compound II
A-60 Table 1, I-180 F group reactive compound II
A-61 Table 1, I-245 A group reactive compound II
A-62 Table 1, I-245 B group reactive compound II
A-63 Table 1, I-245 C group reactive compound II
A-64 Table 1, I-245 D group reactive compound II
A-65 Table 1, I-245 E group reactive compound II
A-66 Table 1, I-245 F group reactive compound II
A-67 Table 1, I-290 A group reactive compound II
A-68 Table 1, I-290 B group reactive compound II
A-69 Table 1, I-290 C group reactive compound II
A-70 Table 1, I-290 D group reactive compound II
A-71 Table 1, I-290 E group reactive compound II
A-72 Table 1, I-290 F group reactive compound II
Above-mentioned reactive compound can also use by agricultural salt with it.These salt are generally alkali metal or alkali salt, as sodium, potassium or calcium salt.
When preparing mixture, the pure reactive compound of preferred use, if required can other reactive compounds as insect, spider or nematode or the weeding as other active components or growth regulating-activity compound or fertilizer mix with antagonism harmful fungoid or other insects using them.
In a preferred embodiment of the invention, azoles the mixture of pyrimidine radicals amine and reactive compound II is used.Under certain conditions, maybe advantageously by azoles and pyrimidine radicals amine and two or more reactive compounds II combine.In addition, the mixture of two or more Compound I and one or more reactive compounds II also may be suitable.
Other active components suitable in above-mentioned meaning especially start mentioned reactive compound II, especially above-mentioned preferred reactive compound.In case of ternary mixtures, preferred 3rd active component is strobilurins class, especially pyraclostrobin, carboxyl acylamide, especially Boscalid, and organic phosphorus compound, especially phosphorous acid and salt thereof.
Compound I and reactive compound II are usually with 100:1-1:100, and preferred 50:1-1:50, preferred 20:1-1:20, especially the weight ratio of 10:1-1:10 uses.
If required, other active components are with 50:1-1:50, and the ratio of preferred 20:1-1:20 adds in Compound I.
Depend on the type of compound and required effect, the rate of application of inventive mixture is 5-2000g/ha, preferred 50-900g/ha, especially 50-750g/ha.
Correspondingly, the rate of application of Compound I is generally 1-1000g/ha, preferred 10-900g/ha, especially 20-750g/ha.
Depend on the type of reactive compound II, the rate of application of reactive compound II is generally 1-2000g/ha, preferred 10-900g/ha, especially 40-500g/ha.
Such as passing through dusting, dressing or soaking in the seed treatment of seed, the rate of application of mixture is generally 1-1000g/100kg seed, preferred 1-750g/100kg, especially 5-500g/100kg.
The method of control harmful fungoid by before or after plant seeding or before or after plant emergence to seed, plant or soil spraying or dusting with separately or the mixture of co-administered Compound I and reactive compound II or Compound I and reactive compound II and carrying out.
Mixture of the present invention or Compound I and reactive compound II can be changed into normal compound agent, such as solution, emulsion, suspension, pulvis, powder, paste and particle.Type of service depends on and is specifically intended to object; Should guarantee that the compounds of this invention is meticulous and distribute equably in each case.
Preparaton is prepared in known manner, such as, by reactive compound is mixed with solvent and/or carrier and prepared, uses emulsifier and dispersant if required.Solvent/the auxiliary agent suitable to this object is mainly:
-water, arsol (as Solvesso product, dimethylbenzene), paraffin (as mineral oil fractions), alcohols (as methyl alcohol, butanols, amylalcohol, benzylalcohol), ketone (as cyclohexanone, gamma-butyrolacton), pyrrolidones (NMP, NOP), acetic acid esters (ethylene acetate), dihydroxylic alcohols, fatty acid dimethylamides, fatty acid and fatty acid ester.Solvent mixture can also be used in principle.
-carrier is as the natural minerals (as kaolin, clay, talcum, chalk) ground and the synthetic mineral (silica, silicate as high degree of dispersion) ground; Emulsifier is if nonionic and anion emulsifier (as polyoxyethylene aliphatic alcohol ether, alkylsulfonate and arylsulphonate) and dispersant are as lignin sulfite waste liquor and methylcellulose.
Suitable surfactant used is lignosulphonic acid, naphthalene sulfonic acids, phenolsulfonic acid, the alkali metal salt of dibutyl naphthalenesulfonic acid, alkali salt and ammonium salt, alkylaryl sulfonates, alkyl sulfate, alkylsulfonate, aliphatic alcohol sulfate, fatty acid and sulphated fatty alcohol glycol ether, also has the condensation product of sulfonated naphthalene and naphthalene derivatives and formaldehyde, the condensation product of naphthalene or naphthalene sulfonic acids and phenol and formaldehyde, NONIN HS 240, ethoxylated isooctyl-phenol, octyl phenol, nonyl phenol, alkyl phenyl polyglycol ether, tributyl phenyl polyglycol ether, three stearyl phenyl polyglycol ethers, alkyl aryl polyether alcohol, alcohol and fatty alcohol/ethylene oxide condensation product, ethoxylated castor oil, polyoxyethylene alkyl ether, ethoxylation polyoxypropylene, laruyl alcohol polyglycol ether acetal, sorbitol ester, lignin sulfite waste liquor and methylcellulose.
Being suitable for preparing the material of Direct spraying solution, emulsion, paste or oil dispersion to be that mid-boiling point arrives high boiling mineral oil fractions, as kerosene or diesel oil, in addition the oil of coal tar and plant or animal origin is also had, aliphatic series, ring-type and aromatic hydrocarbon, such as toluene, dimethylbenzene, paraffin, tetrahydronaphthalene, alkylated naphthalene or derivatives thereof, methyl alcohol, ethanol, propyl alcohol, butanols, cyclohexanol, cyclohexanone, isophorone, intensive polar solvent, such as methyl-sulfoxide, 1-METHYLPYRROLIDONE and water.
Powder, broadcast sowing with material and can dusting product can by active substance being mixed with solid carrier or simultaneous grinding and preparing.
Particle such as coated particle, impregnated granules and homogeneous particle can by adhering to reactive compound and solid carrier and prepare.The example of solid carrier is that ore deposit soil is as silica gel, silicate, talcum, kaolin, activated clay (attaclay), lime stone, lime, chalk, bole, loess, clay, dolomite, diatomite, calcium sulphate, magnesium sulfate, magnesia; The synthetic material ground; Fertilizer is as ammonium sulfate, ammonium phosphate, ammonium nitrate, urea; The product of plant origin as flour, bark powder, wood powder and shuck powder, cellulose powder and other solid carrier.
Formulation for seed treatment additionally can comprise adhesive and/or gelling agent and properly colouring agent.
Preparaton comprises 0.01-95 % by weight usually, the reactive compound of preferred 0.1-90 % by weight.Reactive compound is with 90-100%, and the purity of preferred 95-100% uses.
For seed treatment, described preparaton provides 0.01-60 % by weight, the activity compound concentration of preferred 0.1-40 % by weight in dilution 2-10 doubly rear preparation in sight.
Under be classified as preparaton example of the present invention:
1. the product of dilute with water
A) water-soluble concentrate (SL, LS)
10 weight portion inventive mixture are dissolved in 90 weight parts waters or water-soluble solvent.Or, add wetting agent or other auxiliary agent.Reactive compound dissolves through water dilution.Obtain the preparaton that active compound content is 10 % by weight in this way.
B) dispersed concentrate (DC)
20 weight portion inventive mixture to be dissolved in 70 weight portion cyclohexanone and to add 10 parts per weight dispersing agent as PVP(polyvinyl pyrrolidone).Dilute with water obtains dispersion.Active compound content is 20 % by weight.
C) missible oil (EC)
15 weight portion inventive mixture to be dissolved in 75 parts by weight of xylene and to add calcium dodecyl benzene sulfonate and castor oil ethoxylate (being 5 weight portions in each case).Dilute with water obtains emulsion.The active compound content of this preparaton is 15 % by weight.
D) emulsion (EW, EO, ES)
25 weight portion inventive mixture to be dissolved in 35 parts by weight of xylene and to add calcium dodecyl benzene sulfonate and castor oil ethoxylate (being 5 weight portions in each case).This mixture to be introduced in 30 weight parts waters by mulser (Ultraturrax) and make equal phase emulsion.Dilute with water obtains emulsion.The active compound content of this preparaton is 25 % by weight.
E) suspension (SC, OD, FS)
In the ball mill stirred, 20 weight portion inventive mixture pulverized and adds 10 parts per weight dispersing agent and wetting agent and 70 weight parts waters or organic solvent, obtaining reactive compound suspension in small, broken bits.Dilute with water obtains stable reactive compound suspension.Active compound content in this preparaton is 20 % by weight.
F) water-dispersible granule and water-soluble granular (WG, SG)
The grinding in small, broken bits of 50 weight portion inventive mixture is added 50 parts per weight dispersing agent and wetting agent, is made into water dispersible or water-soluble granular by commercial plant (as extruder, spray tower, fluid bed).Dilute with water obtains stable active compound dispersion or solution.The active compound content of this preparaton is 50 % by weight.
G) water dispersible pow-ders and water-soluble powder (WP, SP, SS, WS)
75 weight portion inventive mixture are ground in rotor-stator grinding machine and adds 25 parts per weight dispersing agent, wetting agent and silica gel.Dilute with water obtains stable active compound dispersion or solution.The active compound content of this preparaton is 75 % by weight.
H) gel formulation
In ball mill, 20 weight portion inventive mixture, 10 parts per weight dispersing agent, 1 weight portion gelling agent and 70 weight parts waters or organic solvent grinding are obtained delicate suspensions.Dilute with water obtains the stable suspension that active compound content is 20 % by weight.
2. the product used without dilution
I) can dusting powder (DP, DS)
The grinding in small, broken bits of 5 weight portion inventive mixture is fully mixed with 95 weight portion kaolin in small, broken bits.This obtain active compound content be 5 % by weight can dusting product.
J) particle (GR, FG, GG, MG)
By the grinding in small, broken bits of 0.5 weight portion inventive mixture and in conjunction with 99.5 weight portion carriers.Current methods be extrude, spraying dry or bed process.This obtains the particle used without dilution that active compound content is 0.5 % by weight.
K) ULV solution (UL)
10 weight portion inventive mixture are dissolved in 90 weight parts organic solvent as in dimethylbenzene.This obtains the product used without dilution that active compound content is 10 % by weight.
For seed treatment, usually use water-soluble concentrate (LS), suspension (FS), can dusting powder (DS), water dispersible and water-soluble powder (WS, SS), emulsion (ES), missible oil (EC) and gel formulation (GF).These preparatons can the form of not diluted or preferably dilution be applied on seed.Use and can carry out prior to seeding.
Preferred use seed treatment FS preparaton.Such preparaton comprises 1-800g reactive compound/l, 1-200g surfactant/l, 0-200g antifreezing agent/l, 0-400g adhesive/l, 0-200g colouring agent/l and solvent usually, preferred water.
The similar preparaton A-K of Compound I or reactive compound II comprises each reactive compound of respective amount.They are being diluted to namely with directly mixing (bucket mixes thing) in the process of activity compound concentration usually before administration.
Reactive compound can change by the concentration in preparation shortly in relative broad range.They are generally 0.0001-10%, preferred 0.01-1%.
Reactive compound can directly, with its preparaton form or type of service prepared therefrom (as can Direct spraying solution, powder, suspension or dispersion, emulsion, oil dispersion, paste, can dusting product, broadcast sowing with material or particle), by spraying, atomization, dusting, broadcast sowing or water and use.Type of service depends on the object be intended to completely; Be intended to guarantee in each case that the best of reactive compound of the present invention may distribute.
Moisture type of service is prepared by emulsion concentrates, paste or wettable powder (sprayable powder, oil dispersion) by adding water.For preparation emulsion, paste or oil dispersion, can by wetting agent, tackifier, dispersant or emulsifier by this material directly or to be dissolved in after in oil or solvent homogenizing in water.But, can also prepare by active substance, wetting agent, tackifier, dispersant or emulsifier and properly solvent or the concentrate that forms of oil and this concentrate is suitable for dilute with water.
Reactive compound also can be used successfully to ultra low volume method (ULV), wherein can use the preparaton comprised more than 95 % by weight reactive compounds, or even uses not containing the reactive compound of additive.
Various types of oil, wetting agent, adjuvant, weed killer herbicide, fungicide, other agricultural chemicals or bactericide can be added in reactive compound, only add before being close to use if required (bucket mixes thing).These reagent usually with the present composition with 1:100-100:1, the weight ratio of preferred 1:10-10:1 mixes.
The polysiloxanes that adjuvant suitable is thus especially organically-modified, such as BreakThruS alcohol alkoxylates, such as Atplus atplusMBA plurafacLF with oN30; EO/PO block polymer, such as rPE2035 and b; Alcohol ethoxylate, such as xP80; And sulfosuccinic acid dioctyl ester sodium, such as rA.
Compound I and II or mixture or corresponding preparaton by with the mixture of effective fungicidal amount or the Compound I in separate administration situation and II process harmful fungoid, need to prevent their plant, seed, soil, region, material or space and use.Use and can carry out before or after infected by harmful fungi.
Application Example
The fungicidal effect of compound and mixture is confirmed by following test:
Reactive compound amisulbrom, Kocide SD, famoxadone, phosphorous acid and zoxamide use with commercially available preparaton and are diluted with water to described concentration.
Use acetone and/or DMSO and emulsifier that solvent/emulsifier volume ratio is 99:1 reactive compound is made and is comprised 25mg reactive compound and the stock solution being made into 10ml by the mixture of EL (having the wetting agent based on ethoxylated alkylphenol of emulsification and peptizaiton) alone or in combination.Then this mixture water is made into 100ml.This stock solution is diluted to following activity compound concentration with described solvent/emulsifier/aqueous mixtures.
The persistence of Application Example 1-to the late blight of tomato that phytophthora infestans causes
Be that the leaf activity compound concentration of the pot plant of " GreatbeeftomatoSt.Pierre " aqueous suspension as described below is sprayed to drip point by cultivar.By the moisture spore suspension inoculation of leaf phytophthora infestans after 5 days.Then plant being placed on temperature is in the steam-laden room of 18-20 DEG C.After 6 days, untreated but late blight on the check plant infected develops into and can measure the degree infecting % by naked eyes.
The leaf area percentage that infects that naked eyes measure is changed into the effect represented relative to the % of untreated control.
Use Abbot formula by calculating effect (E) as follows:
E＝(1-α/β)·100
α corresponds to the fungal infection percentage of process plant, and
β corresponds to the fungal infection percentage of untreated (contrast) plant.
Effect is that infecting of 0 expression process plant is on close level in untreated check plant; Effect is that 100 expression process plants are not infected.
The expection effect of active compound use Colby formula [ColbyS.R., " Synergistic calculating combinations of herbicides is corresponding with antagonism ", Weeds (weeds), 15, 20-22,1967] determine and compare with the effect of observing.
Colby formula: E=x+y – xy/100
Expection effect when E working concentration is the mixture of reactive compound A and B of a and b, represents with the % relative to untreated control,
Effect when x working concentration is the reactive compound A of a, represents with the % relative to untreated control,
Effect when y working concentration is the reactive compound B of b, represents with the % relative to untreated control.
The reactive compound of Table A-independent
The inventive mixture of the reactive compound of table B-table 1
*) effect of Colby formulae discovery is used
The activity of Application Example 2-to the late blight of tomato that phytophthora infestans causes, protectiveness process
Aqueous suspension as described below for the leaf activity compound concentration of potted plant tomato plant is sprayed to drip point.After seven days, the moisture sporangia suspension of leaf phytophthora infestans is infected.Then plant being placed on temperature is in the steam-laden room of 18-20 DEG C.After 6 days, untreated but late blight on the check plant infected develops into and can measure the degree infecting % by naked eyes.
Be similar to embodiment 1 to evaluate.
Application Example 3-to the activity by the mould grape vine downy mildew caused of the raw single shaft of grape
Aqueous suspension as described below for the leaf activity compound concentration of grape pot rattan is sprayed to drip point.With the moisture sporangia suspension inoculation leaf dorsal part that the raw single shaft of grape is mould after 3 days.Then first grape vine is placed in the steam-laden room 24 hours of 24 DEG C, and then in the greenhouse being placed on 20-30 DEG C 5 days.After during this period of time, again this plant to be placed in moist room 16 hours to promote that sporangiophore grows.Then naked eyes determination leaf dorsal part infect development degree.
Be similar to embodiment 1 to evaluate.
Application Example 4-to the activity by the mould grape vine downy mildew caused of the raw single shaft of grape
Aqueous suspension as described below for the leaf activity compound concentration of grape pot rattan is sprayed to drip point.With the moisture sporangia suspension inoculation leaf dorsal part that the raw single shaft of grape is mould after 7 days.Then first grape vine is placed in the steam-laden room 24 hours of 24 DEG C, and then in the greenhouse being placed on 20-30 DEG C 5 days.After during this period of time, again this plant to be placed in moist room 16 hours to promote that sporangiophore grows.Then naked eyes determination leaf dorsal part infect development degree.
Be similar to embodiment 1 to evaluate.
titer plate is tested
Reactive compound is separately mixed with the stock solution that concentration is 10000ppm in DMSO.
The yellow grand and oxime bacterium ester of reactive compound fluazinam, pyraclostrobin, Kocide SD, benzene metsulfovax, phosphorous acid, dodemorfe, zoxamide, sulphur ammonia uses with commercially available preparaton and is diluted with water to described concentration.
The activity of Application Example 5-to late blight pathogene phytophthora infestans in titer plate test
This stock solution pipette is moved on to titer plate (MTP) upper and by moisture pea juice base mycotrophy medium to described activity compound concentration.Then the moisture zoospore suspension of phytophthora infestans is added.Each plate being placed on temperature is in the steam-laden room of 18 DEG C.Absorption spectrophotometry within 7 days, is used to measure each MTP afterwards under 405nm in inoculation.
By the parameter of measurement with not containing the scheme that contrasts of reactive compound growth and do not compare containing the blank value of fungi and reactive compound, to determine the relative growth % of pathogene in each reactive compound.
The activity of Application Example 6-to gray mold pathogene Botrytis cinerea in titer plate test
This stock solution pipette is moved on to titer plate (MTP) upper and by moisture Fructus Hordei Germinatus base mycotrophy medium to described activity compound concentration.Then the moisture spore suspension of Botrytis cinerea is added.Each plate being placed on temperature is in the steam-laden room of 18 DEG C.Absorption spectrophotometry within 7 days, is used to measure each MTP afterwards under 405nm in inoculation.
Be similar to embodiment 5 to evaluate.
The activity of Application Example 7-to rice blast pathogene Pyricularia oryzae in titer plate test
Stock solution is mixed in proportion, to move on in titer plate (MTP) with pipette and by moisture Fructus Hordei Germinatus base mycotrophy medium to described activity compound concentration.Then the moisture spore suspension of Pyricularia oryzae is added.Each plate being placed on temperature is in the steam-laden room of 18 DEG C.Absorption spectrophotometry within 7 days, is used to measure each MTP afterwards under 405nm in inoculation.
Be similar to embodiment 5 to evaluate.
The activity of Application Example 8-to leaf spot pathogene wheat septoria in titer plate test
Stock solution is mixed in proportion, to move on in titer plate (MTP) with pipette and by moisture Fructus Hordei Germinatus base mycotrophy medium to described activity compound concentration.Then the moisture spore suspension of wheat septoria is added.Each plate being placed on temperature is in the steam-laden room of 18 DEG C.Absorption spectrophotometry within 7 days, is used to measure each MTP afterwards under 405nm in inoculation.
Be similar to embodiment 5 to evaluate.
Result of the test shows due to synergistic function, and the effect of inventive mixture is significantly higher than the effect using the expection of Colby formula.

Claims (10)

1. a Fungicidal mixture, it comprises following compound as active component using Synergistic effective dose:
1) azoles of formula I pyrimidine radicals amine:
Wherein each substituting group defined as follows:
R 1for C 3-C 12alkyl, C 2-C 12alkenyl, C 5-C 12alkoxyalkyl, C 3-C 6cycloalkyl, phenyl or phenyl-C 1-C 4alkyl;
R 2for C 1-C 12alkyl, C 2-C 12alkenyl, C 1-C 4haloalkyl, C 1-C 4alkoxy-C 1-C 4alkyl;
Wherein R 1and/or R 2in aliphatic chain can by the identical or different radicals R of 1-4 areplace:
R afor halogen, cyano group, hydroxyl, sulfydryl, C 1-C 10alkyl, C 1-C 10haloalkyl, C 3-C 8cycloalkyl, C 2-C 10alkenyl, C 2-C 10alkynyl, C 1-C 6alkoxyl, C 1-C 6alkylthio group, C 1-C 6alkoxy-C 1-C 6alkyl or NR ar b;
R a, R bfor hydrogen and C 1-C 6alkyl;
Wherein R 1and/or R ain cyclic group can by 1-4 radicals R breplace:
R bfor halogen, cyano group, hydroxyl, sulfydryl, nitro, NR ar b, C 1-C 10alkyl, C 1-C 6haloalkyl, C 2-C 6alkenyl, C 2-C 6alkynyl or C 1-C 6alkoxyl;
R 3for hydrogen, halogen, cyano group, NR ar b, hydroxyl, sulfydryl, C 1-C 6alkyl, C 1-C 6haloalkyl, C 3-C 8cycloalkyl, C 1-C 6alkoxyl, C 1-C 6alkylthio group, C 3-C 8cycloalkyloxy, C 3-C 8cycloalkylthio, carboxyl, formoxyl, C 1-C 10alkyl-carbonyl, C 1-C 10alkoxy carbonyl group, C 2-C 10chain ene keto carbonyl, C 2-C 10alkynes oxygen carbonyl, phenyl, phenoxy group, thiophenyl, benzyloxy, benzylthio,
C 1-C 6alkyl-S (O) m-;
M is 0,1 or 2;
A is CR 3or N;
With
2) at least one is selected from the reactive compound II of following azole: cyproconazole, Flusilazole, ring penta azoles bacterium, propiconazole, prothioconazoles, Tebuconazole, Prochloraz, Guardian;
Wherein component 1) with component 2) weight ratio be 1:20-20:1.
2. Fungicidal mixture according to claim 1, it is the ternary fungicidal mixtures comprising two kinds of reactive compound II.
3., according to the Fungicidal mixture of claim 1 or 2, comprise the formula I corresponding to formula IA:
Wherein
R 1for C 3-C 12alkyl, C 5-C 12alkoxyalkyl, phenyl or phenyl-C 1-C 4alkyl, wherein phenyl can by 1-3 radicals R breplace;
R 2for C 1-C 12alkyl, C 1-C 4haloalkyl, C 1-C 4alkoxy-C 1-C 4alkyl;
R 3for hydrogen or NH 2.
4. a composition, comprises liquid or solid carrier and mixture as claimed in one of claims 1-3.
5. prevent and treat a method for phytopathogenic harmful fungi, wherein prevent the plant of fungal attack, soil or seed with the Compound I according to claim 1 of effective dose and at least one Compound II per process harmful fungoid, its habitat or need,
Wherein said harmful fungoid is the harmful fungoid being selected from Oomycete.
6. method according to claim 5, wherein simultaneously, i.e. associating or separate administration or use Compound I according to claim 1 and II successively.
7., according to the method for claim 5 or 6, wherein use Compound I according to claim 1 and II or mixture as claimed in one of claims 1-3 with the amount of 5-2000g/ha.
8., according to the method for claim 5 or 6, wherein use Compound I according to claim 1 and II or mixture as claimed in one of claims 1-3 with the amount of 1-1000g/100kg seed.
9. process a method for seed, wherein use mixture as claimed in one of claims 1-3 with the amount of 1-1000g/100kg seed.
10. prepare a method for composition according to claim 4, wherein make Compound I according to claim 1 and II mix with liquid or solid carrier.
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